title: Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.
abstract: The scope of palladium-catalyzed, auxiliary-assisted direct arylation and alkylation of sp(2) and sp(3) C-H bonds of amine and carboxylic acid derivatives has been investigated. The method employs a palladium acetate catalyst, substrate, aryl, alkyl, benzyl, or allyl halide, and inorganic base in tert-amyl alcohol or water solvent at 100-140 °C. Aryl and alkyl iodides as well as benzyl and allyl bromides are competent reagents in this transformation. The picolinic acid auxiliary is used for amine γ-functionalization, and the 8-aminoquinoline auxiliary is used for carboxylic acid β-functionalization. Some optimization of base, additives, and solvent is required for achieving best results.
authors.affiliation: Department of Chemistry, University of Houston , Houston, Texas 77204, United States.
authors.forename: Enrico T
authors.initials: ET
authors.lastname: Nadres
authors.forename: Gerson Ivan Franco
authors.initials: GI
authors.lastname: Santos
authors.forename: Dmitry
authors.initials: D
authors.lastname: Shabashov
authors.forename: Olafs
authors.initials: O
authors.lastname: Daugulis
mesh_terms: D000478:Alkylation; D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006860:Hydrogen Bonding; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry
chemical_list: D000634:Aminoquinolines; D002264:Carboxylic Acids; D012997:Solvents; D010165:Palladium; C080436:8-aminoquinoline